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Jerry.ai are hiring a

Sr. Product Designer

You could work anywhere. Why join Jerry?

Jerry is building the first AI-powered assistant for car ownership, making it easy and affordable for the 80% of Americans who rely on their cars every day. From buying and insurance to financing, safety, and repairs, we’re reimagining the entire experience of owning a car. It’s a $2T industry that’s fragmented, analog, and full of friction — and no one else is tackling it end-to-end. Since launching in 2019, over 5 million people have trusted Jerry to manage their car insurance, maintenance, and safety. We reached profitability in 2024, are backed by $240M in funding, and are on track to become a $10B company by 2030.

Customers love what we’ve built, and we’re just getting started. Now we’re ready to elevate our craft, define our brand, and design the next generation of products that make car ownership feel effortless. In other words: we have function. Now we need form.

Why this role matters

Design is how we make car ownership feel easy… and even enjoyable. As a Senior Product Designer, you’ll play a key role in shaping how millions of people interact with Jerry’s core products. You’ll collaborate closely with PMs, engineers, and data scientists to translate complex problems and data into clear, intuitive, and visually polished experiences.

You’ll own end-to-end design. From mapping user flows and crafting wireframes to refining high-fidelity visuals, and using prototypes to bring ideas to life. Your work will help drivers make better decisions about insurance, safety, and repairs with confidence and ease.

What you’ll work on

  • Partner with PMs and engineers to define user problems, simplify data-heavy experiences, and design solutions that drive measurable outcomes.
  • Create user flows, low- and high-fidelity wireframes, prototypes, and final UI for features across Jerry’s core products.
  • Lead UX explorations for complex problems — structuring workflows that make car ownership and management feel simple and intuitive.
  • Leverage research, analytics, and experimentation to inform design decisions and validate your approach.
  • Collaborate with other designers to evolve our design system and raise our craft bar across mobile and web.
  • Thoughtfully apply AI to improve clarity, personalization, and automation in the experience.

Who you’ll work with

You won’t be another cog in a big design machine. You’ll collaborate directly with:

  • Kruise Sapstein – Head of Design, leading Jerry’s product design vision and building a high-performing, high-craft design culture.
  • Art Agrawal – CEO & Head of Product, shaping company direction and customer experience at the highest level.
  • A broader product org of 11 PMs, 55 engineers, and 12 analysts/data scientists, all driven to build a best-in-class consumer experience.

What we’re looking for

  • A portfolio that showcases strong UX thinking, data-informed decision making, and clean, intuitive interface design.
  • 5+ years of experience designing consumer-facing mobile or web products (agency or in-house).
  • Proven ability to translate complex data and product requirements into simple, elegant workflows.
  • Comfortable collaborating with PMs and engineers to define scope, prioritize solutions, and iterate quickly.
  • Skilled in Figma and experienced with rapid prototyping tools to communicate ideas clearly.
  • Understanding of design systems and how to use or evolve them for consistency and scale.
  • Excellent communication skills — able to articulate design rationale clearly to technical and non-technical partners.
  • Bonus: experience in marketplaces, fintech, insurance, or mobility.

While we appreciate your interest and application, only applicants under consideration will be contacted.

About Jerry.ai:

Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.

We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.